Pentachlorobenzenethiol

Pentachlorobenzenethiol
Names
Preferred IUPAC name
Pentachlorobenzenethiol
Other names
Pentachlorobenzenethiol, pentachlorothiophenol, PCBT
Identifiers
CAS Number
  • 133-49-3 checkY
3D model (JSmol)
  • Interactive image
ChemSpider
  • 8301
ECHA InfoCard 100.004.644 Edit this at Wikidata
EC Number
  • 205-107-8
PubChem CID
  • 8620
UNII
  • 92A1Z48VJB checkY
CompTox Dashboard (EPA)
  • DTXSID3044540 Edit this at Wikidata
InChI
  • InChI=1S/C6HCl5S/c7-1-2(8)4(10)6(12)5(11)3(1)9/h12H
    Key: LLMLGZUZTFMXSA-UHFFFAOYSA-N
  • C1(=C(C(=C(C(=C1Cl)Cl)Cl)Cl)Cl)S
Properties
Chemical formula
 C6HCl5S
Molar mass 282.38 g·mol−1
Appearance Gray solid
Density 1.7±0.1 g/cm3
Melting point 231.5 °C (448.7 °F; 504.6 K)
Solubility in water
 Insoluble
Hazards
GHS labelling:
Pictograms
 GHS05: Corrosive
Warning
Flash point 144.6 °C (292.3 °F; 417.8 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references
Chemical compound

Pentachlorobenzenethiol is a chemical compound from the group of thiols and organochlorine compounds.[1] The chemical formula is C
6HCl
5S.[2]

Synthesis

Pentachlorobenzenethiol can be obtained from hexachlorobenzene.[3]

Properties

Pentachlorobenzenethiol is a combustible gray solid with an unpleasant odor, practically insoluble in water. It has a monoclinic crystal structure.[4] The compound is not well-biodegradable and presumably bioaccumulable and toxic for aquatic organisms. Pentachlorobenzenethiol is itself a metabolite of hexachlorobenzene and is found in the urine and the excretions of animals receiving hexachlorobenzene.[5] Pentachlorobenzenethiol has a high potential for long-range transport via air as it is very slowly degraded in atmosphere.[6]

Applications

Pentachlorobenzenethiol is used in the rubber industry. The compound is added to rubber (both natural and synthetic) to facilitate processing (mastication).

See also

References

  1. ^ "Pentachlorobenzenethiol". chemindustry.com. Retrieved 9 June 2017.
  2. ^ "2,3,4,5,6-pentachlorobenzenethiol". Retrieved 9 June 2017.
  3. ^ Kulka, Marshall (1959). "Reaction of Hexachlorobenzene with Mercaptides". J. Org. Chem. 24 (4): 235–237. doi:10.1021/jo01084a021.
  4. ^ Wojcik, G.; Charbonneau, G. P.; Delugeard, Y.; Toupet, L. (1980). "The disordered crystal structure of pentachlorothiophenol". Acta Crystallogr. B36 (2): 506–507. doi:10.1107/S0567740880003706.
  5. ^ Koss, G.; Koransky, W.; Steinbach, K. (June 1976). "Studies on the toxicology of hexachlorobenzene: II. Identification and determination of metabolites". Archives of Toxicology. 35 (2): 107–114. doi:10.1007/BF00372764. PMID 947309. S2CID 25403466.
  6. ^ "TC NES SUBGROUP ON IDENTIFICATION OF PBT AND VPVB SUBSTANCES". EChA. echa.europa.eu. Retrieved 9 June 2017.

External links

  • Preparation of pentachlorothiophenol US 2922820 A